Dichloromethane → N-Methyl-1-(methylsulfonyl)piperidin-3-amine

HRID 28521Notes

Reaction equation

HRID 28521 reaction equation
[CH3:1][NH:2][CH:3]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4]1.[CH3:9][S:10](Cl)(=[O:12])=[O:11].CCN(C(C)C)C(C)C.C(Cl)Cl>[Pd].CCO>[CH3:9][S:10]([N:5]1[CH2:6][CH2:7][CH2:8][CH:3]([NH:2][CH3:1])[CH2:4]1)(=[O:12])=[O:11]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 15670691N-Methylpiperidin-3-amine

Product 1

HCID 21983816N-Methyl-1-(methylsulfonyl)piperidin-3-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-(Methanesulfonyl)-3-(methylamino)piperidine was prepared from N3-Cbz protected 3-methylamino-piperidine: i) CH3S(O)2Cl, i-Pr2NEt, CH2Cl2; ii) H2 (1 atm), 10% Pd/C, EtOH. (m/z): [M+H]+ calcd for C7H16N2O2S 193.10; found, 193.0. 1H-NMR (DMSO-d6; TFA salt): δ (ppm) 3.4 (dd, 1H), 3.2 (m, 2H), 3.10 (s, 3H), 3.0-2.9 (m, 2H), 2.8 (s, 3H), 1.85-1.75 (m, 2H), 1.6-1.4 (m, 2H).

Sources & evidence

ORD record
ord-ff673164c74b471ab6a4166f9c0a5773
Source dataset
uspto-grants-2008_09
Patent number
US07419989B2

Reaction notes

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